Jay will meet people who seek out new and different—and often ridiculous—automotive experiences. He takes funnyman Brad Garrett car shopping to find his perfect automotive match. Jay and comedian Bill Burr go for a spin in Bill's dream sleeper. Later he heads to the racetrack to try a crazy new kind of racing with Tim Allen, and travels to San Francisco to drive a street-legal, flame-breathing motorized snail. All hail the oddball cars, the one-offs, peculiar builds, weird events and those who dare to be different!

Jay checks out vehicles that come close to being perfect; Jon Hamm is treated to a drive down memory lane; Jay and Fabio talk Italian-style while cruising in Fabio's Lamborghini; Jay tries to stump Robert Herjavec.